Benzyl Bromide → 9-Benzyl-6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 1057654Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]1[CH2:12][CH2:11][CH2:10][C:9](=[O:18])[C:8]2=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:14]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9](=[O:18])[C:8]=2[C:7]2[C:15]1=[CH:16][CH:17]=[C:5]([O:4][CH3:3])[CH:6]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a slurry of 60% sodium hydride (0.76 g, 19.6 mmol) in DMF (20 mL) is added 6-methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one (3.84 g, 17.8 mmol) over a period of 5 minutes and benzyl bromide (2.4 mL, 19.6 mmol). The mixture is heated to 50° C. for 1 hour then room temperature overnight. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed with water (200 mL) and concentrated. The residue is triturated in hexanes and filtered to give 4.45 g (80%) of the title compound; mp 174-175° C., IR (drift) 2939, 1633, 1484, 1467, 1448, 1349, 1276, 1242, 1159, 1130, 1099, 854, 791, 762, 710 cm−1. 1H NMR (DMSO-d6) δ2.1, 2., 2.93, 3.75, 5.44, 6.77, 7.09, 7.28, 7.39, 7.51; Anal. Calcd for C20H19NO2: C, 78.66; H, 6.27; N, 4.59. Found: C, 78.45; H, 6.31; N, 4.58.

Workup

customroom temperature overnight
customThe mixture is partitioned between water and CH2Cl2
customThe layers are separated
washthe organic layer washed with water (200 mL)
concentrationconcentrated
customThe residue is triturated in hexanes
filtrationfiltered

Sources & evidence

ORD record: ord-ba9fc0c934af441c8889951a80f68c8e
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514968B1

Reaction notes

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